5-Methylthio-1,3,4-thiadiazol-2-yl isocyanate → HCID 54373746, compound

HRID 436842Notes

Reaction equation

HRID 436842 reaction equation
[CH3:1][S:2][C:3]1[S:7][C:6]([N:8]=[C:9]=[O:10])=[N:5][N:4]=1.[CH2:11]([NH:17][CH2:18][CH:19]=[O:20])[CH2:12][CH2:13][CH:14]=[CH:15][CH3:16]>C1C=CC=CC=1>[CH2:11]([N:17]([CH2:18][CH:19]=[O:20])[C:9]([NH:8][C:6]1[S:7][C:3]([S:2][CH3:1])=[N:4][N:5]=1)=[O:10])[CH2:12][CH2:13][CH:14]=[CH:15][CH3:16]

Participants

4

Reactant 2

HCID 537505795-Methylthio-1,3,4-thiadiazol-2-yl isocyanateHCID 54499301HCID 54499301, compound

Product 1

HCID 54373746HCID 54373746, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 5-methylthio-1,3,4-thiadiazol-2-yl isocyanate dimer (0.05 mole), the diethyl acetal of 2-hex-4-enylaminoacetaldehyde (0.1 mole) and benzene (60 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer and reflux condenser. The reaction mixture is heated at reflux for a period of about 15 minutes. After this time the mixture is stripped of benzene under reduced pressure to yield a solid product as the residue. The residue is then recrystallized to yield the desired product the diethyl acetal of 2-[1-hex-4-enyl-3-(5-methylthio-1,3,4-thiadiazol-2-yl)ureido]acetaldehyde.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. temperatureThe reaction mixture is heated
  4. temperatureat reflux for a period of about 15 minutes
  5. customto yield a solid product as the residue
  6. customThe residue is then recrystallized

Sources & evidence

ORD record
ord-0ddd88be6d5a405088b5b3f381639667
Source dataset
uspto-grants-1977_06
Patent number
US04028375

Reaction notes

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